Painful Rhyme /
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Before we go any further, we must say that Shakespeare created this trope? His rhymes may work today, but that's only because he literally invented a lot of the words and phrases that are common today to justify his use of iambic pentameter. Exactly what this trope page is about. Of course, due to a few centuries of vowel shifting, many Shakespeare rhymes are less painful than they appear to modern ears. "Love" and "prove" rhymed at the time for instance, and as far as anyone can tell, neither of them sounded like they do today.

The Gilbert and Sullivan operettas are full of these. For all of Gilbert's skill at rhyming and willingness to use the entire range of the English language vocabulary, he was not above calling for words to be mispronounced or resorting to substandard English (e.g. "nussed" for "nursed") for the sake of rhyme:

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In The Grand Duke, Gilbert rhymes "lowest" with "gho-est", i.e., a dead person. He hangs a lampshade on this by having the character point this out self-deprecatingly.

When exigence of rhyme compels, Orthography forgoes her spells, And ghost is written ghoest

In The Pirates of Penzance, there is a song "When Frederick was a little lad", in which Ruth describes the troubles that resulted when she confused the similar-sounding words "pilot" and "pirate". They're never actually rhymed with each other, which would be really painful, but that doesn't mean the audience gets off lightly: instead, Ruth pronounces them with unnatural emphasis — "pi-lot" and "pi-rate" — with rhymes to match. (Not to mention the bit where she rhymes "what you people call work" with "maid-of-all-work".)

Also in The Pirates of Penzance, "I Am the Very Model of a Modern Major General" has Stanley singing:

In short, when I've a smattering of elementary strategy... (tries to think of a word to rhyme) You'll say a better Major-General has never sat a-gee!note This means to ride a horse.

Averted if Stanley does an encore of the final verse, in which he simply doesn't even try to rhyme "strategy" and instead flat-out finishes the couplet with "rode a horse".

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Rhyming "die" with "sympathy" (an accepted, if obscure, pronunciation) is bad enough in Patience, but not as bad as when Bunthorne reprises the song in the finale ultimo:

In that case unprecedented, Single I must live and die— I shall have to be contented With a tulip or lily!

I'll be there though I know that it's madness... (blah blah and then...) from the depths of my sadness

or

I should be free, free to be Grace/ So I can feel the wind on my face

Of Thee I Sing has the Senate of the United States slipping into Scottish dialect just to sing a rhyme:

Jilted, jilted, jilted is she— Oh, what is there left but to dee?

Then there's this lovely bit from the patter section of "Love Is Sweeping The Country":

Florida and Cal- Ifornia get together In a festivalOf oranges and weather.

An infamous example is "On the Street Where You Live" from My Fair Lady, which rhymes "bother me" with "rah-ther be."

Conversely, there are several rhymes in My Fair Lady that work with an American accent but not the English accent of the character. (Rhyming "en masse" with "glass", for instance.)

This gets lampshaded in the song "Show Me", when Eliza Doolittle sings, "Haven't your lips/Hungered for mine?/Please don't explain/Show me!" She pronounces "Explain" as "Ex-pline", intentionally falling back on her old flower-girl accent.

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Alan Jay Lerner committed another one in "Come Back To Me", otherwise the best song in On A Clear Day You Can See Forever:

Have you gone to the moon? Or the corner saloon And to rack an' to 'roon'?

That's qualifies as a printed (in the score) Lampshading as far as I'm concerned. ("roon" is supposed to be "ruin" of course

Here's the ring to prove that I'm no joker Thare's 3 ways that love can go That's good, bad or mediocre

Sweet Transvestite has one too:

If you want something visual That's not too abysmal We could take in an old Steve Reeves movie.

The song "Castle on a Cloud" from Les Misérables has a painful non-rhyme (that is, the line isn't supposed to rhyme, but manages to sound as if it was supposed to and didn't):

There is a room that's full of toys, There are a hundred boys and girls.

Also in Les Mis, depending on pronunciation, this rhyme can be quite painful:

Little dear, cost us dear Medicines are expensive, M'sieur

Another Les Mis example comes from "Who Am I":

If I speak, I am condemned If I stay silent, I am damned.

"On My Own" has a couple of these:

In the rain, the pavement shines like silver All the lights are misty in the river

Without him, the world around me changes The trees are bare and everywhere the streets are full of strangers

Wicked contains a few very noticeable clunkers. Special mention should go to "Where so many roam to, / We'll call it home, too" in "One Short Day", and "Dreams the way we planned 'em, / If we work in tandem" in "Defying Gravity".

In "Popular" Galinda corrects the rhyme in a lyric:

Instead of dreary who you were - well, are There's nothing that can stop you from becoming popular - lahr

Boq speaking to Nessa at the Oz Dust dance:

Hey, Nessa Listen Nessa I've got something to confess - aReason why,

In "The Wizard and I", Elphaba sings:

Folks here to an absurd degreeSeem fixated on your verdigris'

And Fiyero in "Dancing Through Life":

Dancing through life Down at the Oz Dust, If only because dustIs what we come to ...

"The Windy City" from Calamity Jane: "Mean wear sideburns, and they oughtta, 'cause a haircut costs a quarter."

"Can I Get a Napkin Please", the song for Improv Everywhere's Food Court Musical, has a couple right in a row: "Got a bunch with your lunch? Got a stack in your pack? Got a couple in your duffel? Got some extras under textbooks?" While the song and performance is awesome and hilarious, these lines come across as totally forced and lame. What the hell do duffels and textbooks have to do with a food court? Thankfully, these lines were cut from the video.

Don't talk about love Or you'll have to say "fits like a glove", Or "as certain as push comes to shove You will pine for the woman you're constantly thinking of." And don't mention your life Or you'll have to say "cuts like a knife", Or refer to the heartbreak and strife When you find that you're missing your wife.

The song "Brush Up Your Shakespeare" from Kiss Me Kate is full of intentionally humourous bad rhymes for Shakespeare plays.

Cole Porter, in general, has written many deliberate mispronunciations of words (and outright non-existent words) into his songs, although not always for the sake of rhyming. "Friendship" from Anything Goes has several of these, including the following "rhyming" couplet:

When other friendships have been for-gate Ours will still be great!

"Paris Makes Me Horny" from the stage version of Victor/Victoria has a lot of terrible rhymes. One could make the argument that the singer (Norma, a rather terrible lounge showgirl singer) would think they are clever. Then, again, it's a Leslie Bricusse lyric, who's been known to write some terrible rhymes before ... tellingly, this song is so poorly regarded that it was cut from at least one subsequent production.

The 1997 TV version of the musical (starring Brandy and Whitney Houston) both featured and lampshaded this trope. When the Fairy Godmother (Houston) first appears, she sings in rhyme, and recites, "Fol-de-rol and fiddle-dee-dee, fiddley-faddley-foodle / All the dreamers in the world are...dizzy in the noodle!" Cinderella (Brandy) replies "That's horrible." The Fairy Godmother, thinking she's talking about the rhyming, defends herself, saying that it's difficult to come up with a spur-of-the-moment couplet. Cinderella was actually referring to the sentiment...although the poetry's not great, either.

A lesser known one comes from Chess, in which the opening number (or closing, depending on your production) contains this little gem:

Though everything they rhyme with Camelot is pretty terrible, the worst possibly being "We're opera-mad in Camelot, we sing from the diaphragm a lot!"

Bonus points should be given to "Something Sort of Grandish" from Finian's Rainbow, which not only intentionally mispronounces words but abbreviates them or makes them up entirely:

Something so dareish So I don't careish, Stirs me from limb to limb. It's so terrifish, magnifish, delish. To have such an amorish glamorish dish.

In "Drop That Name" from Bells Are Ringing, Ella tries to twist "Rin-Tin-Tin" to rhyme with every celebrity's name. She doesn't see how to rhyme it with "Raymond Massey," but fortunately she comes up with the name of anotherHeroic Dog.

In the stage version of Beauty and the Beast, there is an added song after "Be Our Guest" called "If I Can't Love Her" which gives us this rhyme:

Long Ago I Should Have Seen All the Things I could Have Been

In The Desert Song, "One Good Boy Gone Wrong" rhymes "saphead" with "trappéd."

One Touch of Venus features such strained rhymes as warm/ignor'm ("The Trouble With Women"), Rahway/mah way ("Way Out West In Jersey") and memoirs/them was ("Very, Very, Very"). Of course, Ogden Nash was responsible for these lyrics.

So, climb down the chimney It's been a long time since I felt good-neighbor-y Slice up the fruitcake It's time we hung some tinsel on that bayberry bough

Made even more unfortunate by the fact that the "good-neighbor-y" line is sung by Mame's Japanese manservant, Ito, in an apparent stereotypical Asian Speekee Engrish mispronunciation of "good-neighborly".

Jesus Christ Superstar got a new Swedish translation in 2008 and pretty much every single song had examples of this. For instance in Heaven on their Minds one line goes "You have put them under hypnosis/ they're saying Jesus is the son of God''. In Swedish this means rhyming hypnos with Guds son.

"So Long, Farewell" from The Sound of Music painfully twists an English word to fit with a French one:

It's not clear whether again and rain rhymed in Shakespeare's day, but it's painful now.

This is another rhyme that comes down to alternate pronunciations that are valid, but perhaps less used. "Again" can be pronounced either "agen" or "agayn", and only the latter pronunciation rhymes with "rain". If the reader or speaker is used to saying "agen", then the rhyme comes off as quite forced.

Language purists should cringe at the redundant second "in". "In thunder, lightning, or rain" and "In thunder, in lightning, or in rain" are both grammatically logical.

The Wiz has Dorothy sing the following in "Soon As I Get Home", without even trying to force the offending words to sound similar:

Why do I feel like I'm drowning When there is plenty of air? Why do I feel like frowning? I think the feeling is fear.

The movie The Wiz spares viewers from having to hear this "rhyme" by trimming a sizable portion of the song.

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